Sodium Hydroxide → HCID 44606816, compound

HRID 1372574Notes

Reaction equation

HRID 1372574 reaction equation
[F:1][C:2]1[C:10]2[O:9][C:8]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:19][C:20]([O:22]C)=[O:21].[OH-].[Na+]>C1COCC1>[F:1][C:2]1[C:10]2[O:9][C:8]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:19][C:20]([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778451Methyl 7-fluoro-2-(2-methylphenylamino)-6-benzoxazolylacetate

Product 1

HCID 44606816HCID 44606816, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 7-fluoro-2-(2-methylphenylamino)-6-benzoxazolylacetate (1.31 g, 4.17 mmol) was dissolved in THF (30 ml), followed by the addition of 0.25N NaOH (30 ml). The resulting mixture was stirred at room temperature for 20 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. The residue was acidified with 1N HCl, followed by extraction with a chloroform/methanol (10/1) mixture. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, whereby the title compound (1.08 g, 86%) was obtained as a pale brown solid.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. extractionfollowed by extraction with a chloroform/methanol (10/1) mixture
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent, whereby the title compound (1.08 g, 86%)
  8. customwas obtained as a pale brown solid

Sources & evidence

ORD record
ord-b0cd3d13784d44589152c1dad6b10ce4
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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